Imidazole → (4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

HRID 612812

Reaktionsgleichung

Reaktionsgleichung von HRID 612812
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CN=C1.[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C.CCOCC>[C:17]([Si:21]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([CH3:20])([CH3:18])[CH3:19]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 692754-Nitrobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Produkt 1

HCID 15528110(4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-nitrobenzyl alcohol (1.00 g, 6.50 mmol) and imidazole (0.97 g, 14.10 mmol) in DMF (10.0 mL), t-butyl-diphenyl-chlorosilane (1.98 g, 1.87 mL, 7.20 mmol) was added over 10 min under nitrogen at room temperature. The reaction mixture was stirred for an additional 5 h, diluted with 75 mL Et2O, washed with H2O (5 times, 15 mL), dried (MgSO4) and evaporated under vacuum. An oil which crystallised on standing, resulted; yield: 2.54 g. After recrystallisation from EtOH 70%, 2.36 g (93%) of a white soiid is obtained mp 80-81° C. νmax /cm-1 (film): 2931. 2857 (CH2, asym., sym.), 1521. 1345 (NO2); 1H-NMR, δH : 1.06(9H, s, t-Bu), 4.92 (2H, s, CH2), 7.42-7.46 (5H, m, Ph), 7.63-7.65 (7H, m, Ph+Harom2+6), 8.23, (2H, d, J=8.23 Hz, Harom3+5); MS, (EI), (391.54); m/z: 334 (M-t-Bu, 100), 288 (M-t-Bu-NO2, 10), 256 (M-t-Bu-Ph, 20), 199 (Ph2SiOH+, 100); C23H25NO3Si.

Aufarbeitung

  1. washwashed with H2O (5 times, 15 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated under vacuum
  4. customAn oil which crystallised
  5. customresulted
  6. customAfter recrystallisation from EtOH 70%, 2.36 g (93%) of a white soiid
  7. customis obtained mp 80-81° C. νmax /cm-1 (film)

Quellen und Nachweise

ORD-Eintrag
ord-ca54813aa4a94c6d958ac93a77406c0d
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005002

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